This invention is directed to norbornane-2-carboxylic acid esters and in particular to 5(6)-hydroxymethyl-norbornane-2-carboxylic acid esters. These norbornane carboxylic acid esters find utility as intermediates to polyurethanes which are employed as elastomers, coatings and adhesives. Thus, the 5(6)-hydroxymethyl-norbornane-2-carboxylic acid esters can be reacted with polyols to prepare 5(6)-hydroxymethyl-norbornane-2-carboxylic acid polyol esters, which can then subsequently be reacted with polyisocyanates to prepare polyurethanes.
Certain hydroxy-containing norbornane carboxylic acids and esters have previously been known in the chemical literature. Thus, the work of Storm, et al., J.A.C.S. 94:16, pp. 5805-5814, reports the preparation and study of hydroxy-substituted norbornane carboxy compounds to determine the effect of functional group orientation or intramolecular reactions. 2-Hydroxymethyl-bicyclo[2.2.1]heptane-3-carboxylic acid, ethyl ester was prepared as an intermediate in the study of lactonization rates.
It is also known to use hydroxymethyl ester monomers in the preparation of polyurethanes. For example, Peerman, et al., in U.S. Pat. No. 4,423,162 issued Dec. 27, 1983, teaches that hydroxymethyl esters, prepared from naturally occurring fatty oils, can be reacted with polyols and subsequently with polyisocyanates to prepare polyurethanes.